Cheshire, CT 55+ active adult communities & homes for sale

294 homes near Cheshire

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Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

3.6 rating (7 reviews)

Heritage Village

$200Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

No reviews yet

Leisure Village

$200Ks - $500Ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

No reviews yet

The Greens at Half Hollow

$600Ks - $1Ms

The Greens at Half Hollow, Melville, NY

Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes

Want to learn more about 55+ communities in Cheshire? 55places can help!

Questions? Call us: (475) 244-9781

No reviews yet

Rivington

$400Ks - $500Ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

4 rating (1 reviews)

Jefferson Village

$300Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

No reviews yet

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

No reviews yet

The Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

No reviews yet

Meadowbrook Pointe Athlet...

$800Ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

No reviews yet

Leisure Knoll

$300Ks - $500Ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

No reviews yet

Country Pointe Plainview

$1Ms - $1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 homes

5 rating (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

No reviews yet

Leisure Glen

$400Ks - $400Ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

No reviews yet

Spring Lake Village

$200Ks - $200Ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

Want to learn more about 55+ communities in Cheshire? 55places can help!

Questions? Call us: (475) 244-9781

4 rating (8 reviews)

Glenwood Village

$100Ks - $400Ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

3.7 rating (3 reviews)

Greenwood Village

$100Ks - $200Ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

No reviews yet

The Seasons at East Meado...

$500Ks - $600Ks

The Seasons at East Meado..., East Meadow, NY

Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes

No reviews yet

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

No reviews yet

Dutchgate

$400Ks - $400Ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes

No reviews yet

The Waterways at Moriches

$400Ks - $700Ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes

No reviews yet

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

No reviews yet

Overlook

$600Ks - $900Ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

3.5 rating (2 reviews)

Foxwood Village

$300Ks - $400Ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks - $500Ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

Want to learn more about 55+ communities in Cheshire? 55places can help!

Questions? Call us: (475) 244-9781

4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$300Ks - $700Ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks - $800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

No reviews yet

HarborView

$900Ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

No reviews yet

The Club at Melville

$500Ks - $500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

No reviews yet

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

5 rating (1 reviews)

Encore Atlantic Shores

$600Ks - $900Ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

No reviews yet

The Summit at Bethel

$600Ks - $600Ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

4.9 rating (14 reviews)

Chatfield Farms

$600Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

Want to learn more about 55+ communities in Cheshire? 55places can help!

Questions? Call us: (475) 244-9781

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes

No reviews yet

Saddle Lakes

$400Ks - $400Ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

No reviews yet

Country Village Estates

$300Ks - $400Ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $500Ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

423 FLORENCIA PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Want to learn more about 55+ communities in Cheshire? 55places can help!

Questions? Call us: (475) 244-9781

The Seasons at East Meadow

383 SUMMER CT, EAST MEADOW, NY, 11554, East Meadow, NY 11554

$640,000

2 beds

2 baths

1,272 sq ft

Condo

383 SUMMER CT, EAST MEADOW, NY, 11554

Community: The Seasons at East Meadow

Leisure Village

48 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961

$355,000

2 beds

1 baths

1,278 sq ft

Condo

48 TRENT CT B, RIDGE, NY, 11961

Community: Leisure Village

Jefferson Village

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598

$309,900

1 beds

1 baths

800 sq ft

Condo

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10...

Community: Jefferson Village

Jefferson Village

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$574,999

2 beds

2 baths

1,300 sq ft

House

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

New Fairfield at St. James

607 CABOT CT 607, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

1 beds

2 baths

929 sq ft

Condo

607 CABOT CT 607, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Sunken Pond Estates

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$469,000

2 beds

3 baths

1,350 sq ft

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...

Community: Sunken Pond Estates

The Seasons at East Northport

142 AUGUST CIR, EAST NORTHPORT, NY, 1173..., East Northport, NY 11731

$780,302

2 beds

2 baths

1,536 sq ft

Condo

142 AUGUST CIR, EAST NORTHPORT, NY, 1173...

Community: The Seasons at East Northport

Encore Atlantic Shores

167 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941

$955,000

2 beds

3 baths

3,136 sq ft

Condo

167 MELODY CT, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Greenwood Village

57 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$159,999

2 beds

2 baths

1,000 sq ft

Condo

57 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Knoll

304 KINGSTON CT, RIDGE, NY, 11961, Ridge, NY 11961

$429,000

2 beds

2 baths

976 sq ft

Condo

304 KINGSTON CT, RIDGE, NY, 11961

Community: Leisure Knoll

Want to learn more about 55+ communities in Cheshire? 55places can help!

Questions? Call us: (475) 244-9781

Heritage Hills

627 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$525,000

1 beds

2 baths

1,098 sq ft

Condo

627 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

The Seasons at East Northport

116 AUGUST CIR, EAST NORTHPORT, NY, 1173..., East Northport, NY 11731

$780,302

2 beds

2 baths

1,536 sq ft

Condo

116 AUGUST CIR, EAST NORTHPORT, NY, 1173...

Community: The Seasons at East Northport

Stoneleigh Woods at Carmel

505 EGRETS LANDING, CARMEL, NY, 10512, Carmel, NY 10512

$449,900

2 beds

2 baths

1,382 sq ft

Condo

505 EGRETS LANDING, CARMEL, NY, 10512

Community: Stoneleigh Woods at Carmel

Leisure Knoll

151 LAURANCE LN, RIDGE, NY, 11961, Ridge, NY 11961

$399,990

2 beds

1 baths

1,116 sq ft

Condo

151 LAURANCE LN, RIDGE, NY, 11961

Community: Leisure Knoll

New The Vineyards at Miller Place

48 AVERY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$679,900

2 beds

3 baths

1,486 sq ft

Condo

48 AVERY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

Heritage Hills

247 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$389,900

1 beds

1 baths

967 sq ft

Condo

247 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

711 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$499,000

1 beds

2 baths

1,098 sq ft

Condo

711 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Stone Ridge Estates

156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746

$775,000

2 beds

2 baths

1,700 sq ft

Condo

156 CHRISTINE DR, DIX HILLS, NY, 11746

Community: Stone Ridge Estates

Heritage Hills

468 HERITAGE HLS E, SOMERS, NY, 10589, Somers, NY 10589

$599,000

2 beds

2 baths

1,265 sq ft

Condo

468 HERITAGE HLS E, SOMERS, NY, 10589

Community: Heritage Hills

New Fairfield at St. James

501 DREW DR, SAINT JAMES, NY, 11780, Saint James, NY 11780

$429,000

1 beds

2 baths

996 sq ft

Condo

501 DREW DR, SAINT JAMES, NY, 11780

Community: Fairfield at St. James

Want to learn more about 55+ communities in Cheshire? 55places can help!

Questions? Call us: (475) 244-9781

New The Greens at Half Hollow

259 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,599,000

3 beds

4 baths

3,100 sq ft

Condo

259 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Heritage Hills

504 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$615,000

2 beds

2 baths

1,483 sq ft

Condo

504 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

The Villages at Mount Sinai Park

25 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$829,000

2 beds

3 baths

2,229 sq ft

Condo

25 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Stoneleigh Woods at Riverhead

159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$699,999

2 beds

3 baths

2,172 sq ft

House

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Overlook

1040 COTTAGE DR # 26, CARMEL, NY, 10512, Carmel, NY 10512

$799,000

2 beds

2 baths

1,948 sq ft

Condo

1040 COTTAGE DR # 26, CARMEL, NY, 10512

Community: Overlook

Overlook

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051..., Carmel, NY 10512

$689,000

3 beds

4 baths

2,131 sq ft

Condo

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051...

Community: Overlook

Overlook

4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512

$667,000

3 beds

3 baths

1,914 sq ft

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512

Community: Overlook

The Greens at Half Hollow

1126 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$629,888

2 beds

2 baths

1,150 sq ft

Condo

1126 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

1082 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$609,000

2 beds

2 baths

1,000 sq ft

Condo

1082 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Glenwood Village

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901

$229,000

2 beds

2 baths

1,144 sq ft

Mobile Home

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...

Condo

37 HALLEY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

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Frequently Asked Questions

What size 55+ communities are there in Cheshire?

In Cheshire, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Cheshire?

The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.

Are there gated 55+ communities in Cheshire?

No, there are no gated 55+ communities in Cheshire.

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Want to learn more about 55+ communities in Cheshire?

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294 homes near Cheshire

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Cheshire, CT 55+ active adult communities & homes for sale

128 communities near Cheshire

294 homes near Cheshire

2 beds

3 baths

2,496 sq ft

Condo

3 beds

3 baths

1,914 sq ft

Condo

2 beds

3 baths

2,496 sq ft

Condo

2 beds

2 baths

1,140 sq ft

House

3 beds

3 baths

2,500 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

2 beds

1 baths

1,278 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,300 sq ft

House

1 beds

2 baths

929 sq ft

Condo

2 beds

3 baths

1,350 sq ft

Condo

2 beds

2 baths

1,536 sq ft

Condo

2 beds

3 baths

3,136 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

976 sq ft

Condo

1 beds

2 baths

1,098 sq ft

Condo

2 beds

2 baths

1,536 sq ft

Condo

2 beds

2 baths

1,382 sq ft

Condo

2 beds

1 baths

1,116 sq ft

Condo

2 beds